1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene, also known as canagliflozin, belongs to a novel therapeutic class of sodium-glucose co-transporter 2 inhibitors. US drug regulatory approval was received in March 2013 (INVOKANA™) for canagliflozin as an adjunct to diet and exercise to improve glycemic control in adults with type-2 diabetes mellitus. 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene is represented by the following general formula (I):

WO 2005/012326 A1 discloses the compound of formula (I) per se. A procedure for the preparation of the compound of formula (I) is disclosed generically in example 1 of the same application. However, the application is silent about the solid state form obtained.
WO 2008/069327 A1 discloses a crystalline hemihydrate of the compound of formula (I) and a process for the preparation thereof.
WO 2009/035969 A1 discloses a crystalline form of the compound of formula (I). An overlay of the X-ray powder diffractograms of the crystalline form of the compound of formula (I) provided in FIG. 1 of WO 2009/035969 A1 and the crystalline form of the compound of formula (I) provided in FIG. 1 of WO 2008/069327 A1 shows good agreement, confirming the presence of the same solid state form, namely the crystalline hemihydrate. In addition a process for preparing the crystalline hemihydrate of the compound of formula (I) is disclosed. WO 2010/043682 A2 discloses a process for preparing the crystalline hemihydrate of the compound of formula (I).
WO 2011/003976 A1 discloses a process for preparing the crystalline hemihydrate of the compound of formula (I) having a narrow particle size distribution, wherein a suspension of the hemihydrate of formula (I) in an organic solvent or a mixture of an organic solvent and water is subjected to at least one temperature oscillation and at least one mechanical particle size reduction step.
WO 2012/154812 A1 discloses co-crystals of the compound of formula (I) with L-proline and citric acid and methods for their preparation.
WO 2013/064909 A2 discloses amorphous 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene as well as co-crystals of the compound of formula (I) with L-proline, D-proline and L-phenylalanine. Processes for the preparation of these solid forms are also disclosed in the application.
According to the prior art literature, 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene hemihydrate is obtained by crystallization/precipitation from an organic solvent containing some water and optionally an organic antisolvent. However, the use of organic solvents and organic antisolvents in crystallization processes is associated with certain drawbacks as they are often expensive, toxic and/or harmful to health and/or the environment. In addition, residual organic solvents are often not completely removed from active pharmaceutical ingredients by practical manufacturing techniques. Nevertheless, they should be decreased to a minimum amount as these residual solvents show no therapeutic effect and are mostly toxic. Therefore, an environmentally friendly crystallization process for the preparation of crystalline 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene free of organic solvents and consequently a product obtained from this process lacking residual organic solvents is highly desirable.
Furthermore, WO 2008/069327 A1 mentions that amorphous 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene suffers from stability and handling issues such as poor filterability. Therefore, crystalline 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene is preferred since it is, for example, more stable and easier to isolate. In addition, the bioavailability of a compound intended to be administered orally is dependent on the compound's solubility and permeability according to the Biopharmaceutical Classification System. Thus a crystalline form of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene having increased solubility and consequently increased oral bioavailability is desirable.